Dimethylformamide → N-(1-butanesulfonyl)-4-acetylamino-3-nitrobenzamide

HRID 1699640

Reaktionsgleichung

Reaktionsgleichung von HRID 1699640
CN(C)C=O.[C:6]([NH:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][C:11]=1[N+:19]([O-:21])=[O:20])(=[O:8])[CH3:7].[CH2:22]([S:26]([NH2:29])(=[O:28])=[O:27])[CH2:23][CH2:24][CH3:25].C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1>O.C(Cl)(Cl)Cl>[CH2:22]([S:26]([NH:29][C:14](=[O:16])[C:13]1[CH:17]=[CH:18][C:10]([NH:9][C:6](=[O:8])[CH3:7])=[C:11]([N+:19]([O-:21])=[O:20])[CH:12]=1)(=[O:28])=[O:27])[CH2:23][CH2:24][CH3:25]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 184601-ButanesulfonamideHCID 737584-Acetamido-3-nitrobenzoic acidHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene

Produkt 1

HCID 18680978N-(1-butanesulfonyl)-4-acetylamino-3-nitrobenzamideAusbeute 70,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

N,N′-carbonyldiimidazole (9.40 g) is added to an N,N-dimethylformamide (300 ml) solution of 4-acetylamino-3-nitro-benzoic acid (10.0 g), and the solution is stirred for 1 hour at room temperature. Then, 1-butanesulfonamide (7.92 g) and diazabicycloundecene (8.83 g) are added into the solution, and the solution is stirred for 72 hours at 100° C. After chloroform and water are added into the solution and the solution is separated into layers, the residue, which is obtained by concentrating the organic layer, is purified using silica gel column chromatography (eluate: ethyl acetate/methanol=4/1), and thus, N-(1-butanesulfonyl)-4-acetylamino-3-nitrobenzamide (10.75 g) is obtained. 1H-NMR (DMSO-d6, δ): 0.87 (3H, t, J=7.4 Hz), 1.37-1.44 (2H, m), 1.64-1.71 (2H, m), 2.12 (3H, s), 3.52 (2H, t, J=7.7 Hz), 7.83 (1H, d, J=8.6 Hz), 8.21 (1H, dd, J=8.6 and 2.1 Hz), 8.54 (1H, d, J=2.2 Hz), 10.56 (1H, s), 12.32 (1H, s).

Aufarbeitung

  1. stirringthe solution is stirred for 72 hours at 100° C
  2. customthe solution is separated into layers
  3. customthe residue, which is obtained
  4. concentrationby concentrating the organic layer
  5. customis purified

Quellen und Nachweise

ORD-Eintrag
ord-c6b5408aa689489d99c4c281a89c5861
Quelldatensatz
uspto-grants-2002_02
Patentnummer
US06348032B1

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